#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/56/4025667.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025667
loop_
_publ_author_name
'Motonori Watanabe'
'Kenta Goto'
'Masahiko Shibahara'
'Teruo Shinmyozu'
_publ_section_title
;
 Synthesis, Structure, and Electronic and Photophysical Properties of Two-
 and Three-Layered [3.3]Paracyclophane-Based Donor-Acceptor Systems(1)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6104
_journal_page_last               6114
_journal_paper_doi               10.1021/jo100688m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C18 H14 N2 O2 S '
_chemical_formula_sum            'C18 H14 N2 O2 S'
_chemical_formula_weight         322.38
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_audit_creation_date             'Tue Oct 21 17:55:44 2008'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.288(5)
_cell_length_b                   14.087(7)
_cell_length_c                   11.250(7)
_cell_measurement_reflns_used    12304
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     1472.0(14)
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR97
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14435
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_size_max          1.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1742
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                1368
_reflns_number_total             1742
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo100688m_si_003.cif
_cod_data_source_block           General
_cod_original_cell_volume        1471(2)
_cod_original_formula_sum        'C18 H14 N2 O2 S '
_cod_database_code               4025667
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2+x,1/2-y,1/2-z
-x,1/2+y,-z
1/2-x,-y,1/2+z
-x,-y,-z
1/2-x,1/2+y,1/2+z
x,1/2-y,z
1/2+x,y,1/2-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S(1) S 0.33504(6) 0.2500 0.06134(6) 0.0302(2) Uani 1.00 d S . .
O(1) O 0.8586(1) -0.01394(9) -0.1531(1) 0.0389(3) Uani 1.00 d . . .
N(1) N 0.4109(1) 0.16126(9) -0.0051(1) 0.0269(3) Uani 1.00 d . . .
C(1) C 0.7927(2) 0.0435(1) 0.0387(2) 0.0262(4) Uani 1.00 d . . .
C(2) C 0.7650(1) 0.01959(10) -0.0918(1) 0.0256(4) Uani 1.00 d . . .
C(3) C 0.6172(1) 0.0413(1) -0.1456(2) 0.0261(4) Uani 1.00 d . . .
C(4) C 0.5961(1) 0.1469(1) -0.1617(1) 0.0234(3) Uani 1.00 d . . .
C(5) C 0.6736(1) 0.1992(1) -0.2412(1) 0.0267(4) Uani 1.00 d . . .
C(6) C 0.5025(1) 0.19895(10) -0.0855(1) 0.0221(3) Uani 1.00 d . . .
C(7) C 0.9100(1) 0.2005(1) -0.0098(2) 0.0270(4) Uani 1.00 d . . .
C(8) C 0.8098(1) 0.1503(1) 0.0573(1) 0.0226(3) Uani 1.00 d . . .
C(9) C 0.7205(1) 0.2001(1) 0.1344(1) 0.0240(4) Uani 1.00 d . . .
H(1) H 0.889(2) 0.006(1) 0.061(2) 0.040(5) Uiso 1.00 calc . . .
H(2) H 0.717(2) 0.021(1) 0.094(2) 0.036(5) Uiso 1.00 calc . . .
H(3) H 0.611(2) 0.007(1) -0.222(2) 0.034(4) Uiso 1.00 calc . . .
H(4) H 0.542(2) 0.019(1) -0.092(2) 0.030(4) Uiso 1.00 calc . . .
H(5) H 0.735(2) 0.170(1) -0.294(2) 0.032(4) Uiso 1.00 calc . . .
H(6) H 0.975(2) 0.169(1) -0.060(1) 0.031(4) Uiso 1.00 calc . . .
H(7) H 0.655(2) 0.167(1) 0.188(2) 0.034(4) Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N(1) S(1) N(1) 101.15(9) . . 7_555 yes
S(1) N(1) C(6) 106.27(10) . . . yes
C(2) C(1) C(8) 111.5(1) . . . yes
O(1) C(2) C(1) 121.0(1) . . . yes
O(1) C(2) C(3) 119.9(2) . . . yes
C(1) C(2) C(3) 119.1(1) . . . yes
C(2) C(3) C(4) 111.1(1) . . . yes
C(3) C(4) C(5) 122.8(1) . . . yes
C(3) C(4) C(6) 121.0(1) . . . yes
C(5) C(4) C(6) 116.0(1) . . . yes
C(4) C(5) C(5) 122.67(9) . . 7_555 yes
N(1) C(6) C(4) 125.8(1) . . . yes
N(1) C(6) C(6) 113.16(8) . . 7_555 yes
C(4) C(6) C(6) 120.99(8) . . 7_555 yes
C(7) C(7) C(8) 120.54(9) 7_555 . . yes
C(1) C(8) C(7) 119.7(1) . . . yes
C(1) C(8) C(9) 121.4(1) . . . yes
C(7) C(8) C(9) 118.8(1) . . . yes
C(8) C(9) C(9) 120.32(8) . . 7_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) N(1) 1.618(1) . . yes
S(1) N(1) 1.618(1) . 7_555 yes
O(1) C(2) 1.206(2) . . yes
N(1) C(6) 1.350(2) . . yes
C(1) C(2) 1.528(2) . . yes
C(1) C(8) 1.527(2) . . yes
C(2) C(3) 1.531(2) . . yes
C(3) C(4) 1.511(2) . . yes
C(4) C(5) 1.364(2) . . yes
C(4) C(6) 1.423(2) . . yes
C(5) C(5) 1.431(3) . 7_555 yes
C(6) C(6) 1.438(3) . 7_555 yes
C(7) C(7) 1.395(3) . 7_555 yes
C(7) C(8) 1.391(2) . . yes
C(8) C(9) 1.390(2) . . yes
C(9) C(9) 1.405(3) . 7_555 yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) C(3) 3.392(2) . 8_554 ?
O(1) C(1) 3.510(2) . 5_755 ?
N(1) C(2) 3.217(2) . 5_655 ?
N(1) C(3) 3.330(2) . 5_655 ?
N(1) C(1) 3.470(2) . 5_655 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S(1) N(1) C(6) C(4) 177.7(1) . . . . yes
S(1) N(1) C(6) C(6) 0.06(10) . . . 7_555 yes
S(1) N(1) C(6) C(4) -177.7(1) . 7_555 7_555 7_555 yes
S(1) N(1) C(6) C(6) -0.06(10) . 7_555 7_555 . yes
O(1) C(2) C(1) C(8) 104.6(2) . . . . yes
O(1) C(2) C(3) C(4) -106.6(2) . . . . yes
N(1) S(1) N(1) C(6) 0.1(1) . . 7_555 7_555 yes
N(1) C(6) C(4) C(3) -9.4(2) . . . . yes
N(1) C(6) C(4) C(5) 176.3(1) . . . . yes
N(1) C(6) C(6) N(1) 0.0 . . 7_555 7_555 yes
N(1) C(6) C(6) C(4) 177.8(1) . . 7_555 7_555 yes
C(1) C(2) C(3) C(4) 71.7(2) . . . . yes
C(1) C(8) C(7) C(7) 168.57(9) . . . 7_555 yes
C(1) C(8) C(9) C(9) -168.51(10) . . . 7_555 yes
C(2) C(1) C(8) C(7) -53.7(2) . . . . yes
C(2) C(1) C(8) C(9) 121.9(2) . . . . yes
C(2) C(3) C(4) C(5) 67.5(2) . . . . yes
C(2) C(3) C(4) C(6) -106.5(2) . . . . yes
C(3) C(2) C(1) C(8) -73.7(2) . . . . yes
C(3) C(4) C(5) C(5) -167.90(10) . . . 7_555 yes
C(3) C(4) C(6) C(6) 168.13(9) . . . 7_555 yes
C(4) C(5) C(5) C(4) 0.0 . . 7_555 7_555 yes
C(4) C(6) C(6) C(4) 0.0 . . 7_555 7_555 yes
C(5) C(4) C(6) C(6) -6.2(1) . . . 7_555 yes
C(5) C(5) C(4) C(6) -6.3(1) . 7_555 7_555 7_555 yes
C(7) C(7) C(8) C(9) 7.1(2) . 7_555 7_555 7_555 yes
C(7) C(8) C(9) C(9) 7.1(2) . . . 7_555 yes
C(8) C(7) C(7) C(8) 0.0 . . 7_555 7_555 yes
C(8) C(9) C(9) C(8) 0.0 . . 7_555 7_555 yes
C(8) C(9) C(9) C(8) 0.0 . . 7_555 7_555 yes
